Regiospecific Synthesis of Tetra-Substituted Furans

Leiv K. Sydnes, Rustem Isanov, Myagmarsuren Sengee, Francesco Livi

Research output: Contribution to journalJournal articleResearchpeer-review

1 Downloads (Pure)

Abstract

α,β-Unsaturated acetylenic γ-hydroxyketones have been shown to react with ethyl acetoacetate in a Michael-addition fashion and subsequently undergo cyclization followed by dehydration to give substituted furans with a predictable regiospecificity. The yields were good to excellent. A mechanism for the transformation is proposed, and this mechanism explains why furan formation does not take place when the same unsaturated ketones are treated with α-methylated acetoacetate and diethyl malonate.
Original languageEnglish
JournalSynthetic Communications
Volume43
Issue number21
Pages (from-to)2898-2905
ISSN0039-7911
DOIs
Publication statusPublished - 2013
Externally publishedYes

Bibliographical note

Supplementary materials are available for this article. Go to the publisher’s online edition of Synthetic Communications1 for the following free supplemental resource: Full experimental and spectral details.

Keywords

  • Conjugated acetylenic ketones
  • Ketoesters
  • Propargylic alcohols

Cite this

Sydnes, L. K., Isanov, R., Sengee, M., & Livi, F. (2013). Regiospecific Synthesis of Tetra-Substituted Furans. Synthetic Communications, 43(21), 2898-2905. https://doi.org/10.1080/00397911.2012.748076